Acta Cryst. (2011). E67, m1396 [ doi:10.1107/S1600536811037160 ]
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2N7,N8]diiodidomercury(II)In the title compound, [HgI2(C23H14N4O)], the HgII atom is four-coordinated by two N atoms from one 1-(1H-imidazo[4,5-f][1,10]phenanthrolin-2-yl)naphthalen-2-ol ligand and by two I atoms in a distorted tetrahedral environment. An intramolecular O-H
N hydrogen bond stabilizes the molecular conformation and an intermolecular N-HI interaction stabilizes the crystal packing.
A mixture of HgI2 (0.5 mmol) and 1-(1H-imidazo[4,5-f][1,10]phenanthrolin-2-yl)naphthalen-2-ol) (0.5 mmol) in 8 mL distilled water was heated at 462 K in a Teflon-lined stainless steel autoclave for seven days. The reaction system was then slowly cooled to room temperature. Pale yellow crystals of the title compound suitable for single crystal X-ray diffraction analysis were collected from the final reaction system by filtration, washed several times with distilled water and dried in air at ambient temperature. Yield: 15% based on Hg(II).
H atoms bonded to N and C were positioned geometrically (C-H = 0.93 Å) and refined as riding, with Uiso(H)=1.2Ueq(carrier). The H atom bonded to O was freely refined.
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).
![[Figure 1]](./bt5643fig1thm.gif)
| Fig. 1. Perspective view of the title compound, showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. |
| [HgI2(C23H14N4O)] | F(000) = 1496 |
| Mr = 816.77 | Dx = 2.444 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2ybc | Cell parameters from 4351 reflections |
| a = 14.4271 (10) Å | θ = 1.9–26.0° |
| b = 7.3026 (5) Å | µ = 9.74 mm−1 |
| c = 21.1337 (15) Å | T = 293 K |
| β = 94.472 (1)° | Block, pale yellow |
| V = 2219.8 (3) Å3 | 0.17 × 0.14 × 0.12 mm |
| Z = 4 |
| Bruker SMART APEX diffractometer | 4351 independent reflections |
| Radiation source: fine-focus sealed tube | 3217 reflections with I > 2σ(I) |
| graphite | Rint = 0.031 |
| φ and ω scans | θmax = 26.0°, θmin = 1.9° |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −16→17 |
| Tmin = 0.41, Tmax = 0.64 | k = −7→9 |
| 11586 measured reflections | l = −25→26 |
| Refinement on F2 | Primary atom site location: structure-invariant direct methods |
| Least-squares matrix: full | Secondary atom site location: difference Fourier map |
| R[F2 > 2σ(F2)] = 0.029 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.057 | H atoms treated by a mixture of independent and constrained refinement |
| S = 1.01 | w = 1/[σ2(Fo2) + (0.0207P)2 + 0.5359P] where P = (Fo2 + 2Fc2)/3 |
| 4351 reflections | (Δ/σ)max = 0.002 |
| 284 parameters | Δρmax = 0.67 e Å−3 |
| 0 restraints | Δρmin = −0.84 e Å−3 |
| [HgI2(C23H14N4O)] | V = 2219.8 (3) Å3 |
| Mr = 816.77 | Z = 4 |
| Monoclinic, P21/c | Mo Kα radiation |
| a = 14.4271 (10) Å | µ = 9.74 mm−1 |
| b = 7.3026 (5) Å | T = 293 K |
| c = 21.1337 (15) Å | 0.17 × 0.14 × 0.12 mm |
| β = 94.472 (1)° |
| Bruker SMART APEX diffractometer | 4351 independent reflections |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 3217 reflections with I > 2σ(I) |
| Tmin = 0.41, Tmax = 0.64 | Rint = 0.031 |
| 11586 measured reflections | θmax = 26.0° |
| R[F2 > 2σ(F2)] = 0.029 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.057 | Δρmax = 0.67 e Å−3 |
| S = 1.01 | Δρmin = −0.84 e Å−3 |
| 4351 reflections | Absolute structure: ? |
| 284 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
| x | y | z | Uiso*/Ueq | ||
| C2 | 0.8132 (4) | 0.3909 (8) | −0.2038 (3) | 0.0445 (14) | |
| H2 | 0.8549 | 0.3558 | −0.2330 | 0.053* | |
| C7 | 0.6301 (4) | 0.7203 (7) | 0.0288 (2) | 0.0479 (15) | |
| H7 | 0.6592 | 0.7552 | 0.0677 | 0.058* | |
| C8 | 0.5367 (4) | 0.7611 (8) | 0.0162 (2) | 0.0465 (14) | |
| H8 | 0.5047 | 0.8245 | 0.0459 | 0.056* | |
| C9 | 0.4920 (4) | 0.7077 (7) | −0.0400 (2) | 0.0387 (13) | |
| H9 | 0.4290 | 0.7309 | −0.0488 | 0.046* | |
| C10 | 0.5440 (3) | 0.6156 (6) | −0.0847 (2) | 0.0292 (11) | |
| C11 | 0.5070 (3) | 0.5568 (6) | −0.1458 (2) | 0.0291 (11) | |
| C13 | 0.4226 (3) | 0.4818 (6) | −0.2345 (2) | 0.0308 (11) | |
| C14 | 0.3454 (3) | 0.4641 (7) | −0.2832 (2) | 0.0344 (12) | |
| C15 | 0.3641 (4) | 0.5059 (7) | −0.3451 (2) | 0.0434 (13) | |
| C16 | 0.2540 (4) | 0.4097 (8) | −0.2700 (3) | 0.0424 (14) | |
| C17 | 0.2914 (5) | 0.5155 (8) | −0.3934 (3) | 0.0595 (18) | |
| H17 | 0.3039 | 0.5523 | −0.4340 | 0.071* | |
| C18 | 0.2032 (5) | 0.4714 (8) | −0.3811 (3) | 0.0593 (18) | |
| H18 | 0.1557 | 0.4787 | −0.4133 | 0.071* | |
| C19 | 0.1830 (4) | 0.4155 (8) | −0.3208 (3) | 0.0546 (17) | |
| C20 | 0.0924 (5) | 0.3593 (10) | −0.3092 (4) | 0.083 (2) | |
| H20 | 0.0451 | 0.3663 | −0.3416 | 0.099* | |
| C21 | 0.0735 (5) | 0.2951 (11) | −0.2514 (5) | 0.090 (3) | |
| H21 | 0.0131 | 0.2589 | −0.2448 | 0.108* | |
| C22 | 0.1429 (5) | 0.2820 (10) | −0.2013 (3) | 0.075 (2) | |
| H22 | 0.1294 | 0.2351 | −0.1621 | 0.091* | |
| C23 | 0.2314 (4) | 0.3399 (8) | −0.2110 (3) | 0.0563 (17) | |
| H23 | 0.2775 | 0.3327 | −0.1778 | 0.068* | |
| N3 | 0.4179 (3) | 0.5490 (5) | −0.17388 (18) | 0.0316 (10) | |
| H3A | 0.3681 | 0.5804 | −0.1567 | 0.038* | |
| O1 | 0.4506 (3) | 0.5473 (6) | −0.36141 (19) | 0.0563 (11) | |
| H1A | 0.488 (5) | 0.518 (10) | −0.326 (4) | 0.12 (3)* | |
| C1 | 0.8439 (4) | 0.4232 (8) | −0.1411 (3) | 0.0466 (14) | |
| H1 | 0.9066 | 0.4048 | −0.1290 | 0.056* | |
| C3 | 0.7213 (4) | 0.4112 (7) | −0.2222 (2) | 0.0395 (13) | |
| H3 | 0.6990 | 0.3871 | −0.2639 | 0.047* | |
| C4 | 0.6609 (3) | 0.4691 (6) | −0.1774 (2) | 0.0313 (11) | |
| C5 | 0.6970 (3) | 0.5071 (6) | −0.1156 (2) | 0.0323 (11) | |
| C6 | 0.6386 (3) | 0.5855 (6) | −0.0694 (2) | 0.0298 (11) | |
| C12 | 0.5631 (3) | 0.4922 (6) | −0.1909 (2) | 0.0301 (11) | |
| N1 | 0.6800 (3) | 0.6338 (6) | −0.01211 (19) | 0.0390 (11) | |
| N2 | 0.7895 (3) | 0.4787 (5) | −0.09743 (19) | 0.0375 (10) | |
| N4 | 0.5108 (3) | 0.4486 (5) | −0.24611 (18) | 0.0316 (10) | |
| Hg1 | 0.837535 (16) | 0.50252 (3) | 0.013119 (11) | 0.05187 (8) | |
| I1 | 0.78377 (3) | 0.23045 (5) | 0.087966 (19) | 0.05635 (12) | |
| I2 | 0.96077 (3) | 0.77042 (5) | 0.026201 (19) | 0.05224 (12) |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| C2 | 0.039 (3) | 0.053 (4) | 0.043 (3) | 0.006 (3) | 0.014 (3) | 0.005 (3) |
| C7 | 0.070 (4) | 0.047 (4) | 0.026 (3) | −0.011 (3) | 0.003 (3) | −0.006 (3) |
| C8 | 0.064 (4) | 0.047 (4) | 0.029 (3) | 0.001 (3) | 0.010 (3) | −0.004 (3) |
| C9 | 0.041 (3) | 0.041 (3) | 0.035 (3) | 0.005 (2) | 0.013 (2) | 0.003 (3) |
| C10 | 0.035 (3) | 0.026 (3) | 0.027 (3) | −0.002 (2) | 0.003 (2) | 0.004 (2) |
| C11 | 0.029 (3) | 0.033 (3) | 0.025 (3) | 0.000 (2) | 0.003 (2) | 0.001 (2) |
| C13 | 0.042 (3) | 0.026 (3) | 0.025 (2) | −0.003 (2) | 0.005 (2) | 0.002 (2) |
| C14 | 0.040 (3) | 0.037 (3) | 0.026 (3) | 0.000 (2) | 0.002 (2) | −0.003 (2) |
| C15 | 0.060 (4) | 0.033 (3) | 0.035 (3) | 0.006 (3) | −0.007 (3) | −0.003 (3) |
| C16 | 0.037 (3) | 0.044 (3) | 0.046 (3) | 0.007 (3) | 0.000 (3) | −0.015 (3) |
| C17 | 0.099 (6) | 0.042 (4) | 0.034 (3) | 0.013 (4) | −0.015 (3) | −0.005 (3) |
| C18 | 0.073 (5) | 0.049 (4) | 0.050 (4) | 0.018 (3) | −0.029 (3) | −0.016 (3) |
| C19 | 0.046 (4) | 0.044 (4) | 0.070 (5) | 0.015 (3) | −0.020 (3) | −0.021 (3) |
| C20 | 0.043 (5) | 0.086 (6) | 0.115 (7) | 0.014 (4) | −0.016 (4) | −0.039 (5) |
| C21 | 0.037 (4) | 0.095 (6) | 0.140 (8) | −0.002 (4) | 0.018 (5) | −0.048 (6) |
| C22 | 0.060 (5) | 0.094 (6) | 0.077 (5) | −0.018 (4) | 0.033 (4) | −0.033 (4) |
| C23 | 0.049 (4) | 0.071 (4) | 0.051 (4) | −0.009 (3) | 0.013 (3) | −0.024 (3) |
| N3 | 0.035 (2) | 0.034 (2) | 0.026 (2) | −0.0019 (18) | 0.0057 (18) | −0.0040 (18) |
| O1 | 0.071 (3) | 0.066 (3) | 0.033 (2) | −0.006 (2) | 0.012 (2) | 0.001 (2) |
| C1 | 0.029 (3) | 0.058 (4) | 0.052 (4) | 0.003 (3) | 0.004 (3) | 0.007 (3) |
| C3 | 0.042 (3) | 0.042 (3) | 0.035 (3) | 0.004 (2) | 0.005 (3) | −0.001 (3) |
| C4 | 0.033 (3) | 0.030 (3) | 0.031 (3) | 0.000 (2) | 0.006 (2) | 0.002 (2) |
| C5 | 0.034 (3) | 0.024 (3) | 0.038 (3) | −0.002 (2) | 0.002 (2) | 0.003 (2) |
| C6 | 0.039 (3) | 0.027 (3) | 0.024 (3) | −0.006 (2) | 0.002 (2) | 0.006 (2) |
| C12 | 0.034 (3) | 0.028 (3) | 0.028 (3) | −0.002 (2) | 0.002 (2) | 0.001 (2) |
| N1 | 0.047 (3) | 0.038 (3) | 0.031 (2) | −0.006 (2) | −0.004 (2) | 0.003 (2) |
| N2 | 0.032 (2) | 0.040 (3) | 0.040 (2) | 0.000 (2) | −0.0001 (19) | 0.004 (2) |
| N4 | 0.033 (2) | 0.037 (2) | 0.025 (2) | −0.0007 (18) | 0.0039 (18) | −0.0021 (18) |
| Hg1 | 0.04968 (14) | 0.05769 (16) | 0.04649 (14) | −0.01629 (12) | −0.00742 (10) | 0.00740 (13) |
| I1 | 0.0555 (2) | 0.0551 (3) | 0.0607 (3) | 0.00396 (19) | 0.0187 (2) | 0.0143 (2) |
| I2 | 0.0464 (2) | 0.0458 (2) | 0.0623 (3) | −0.00957 (18) | −0.00981 (18) | 0.0071 (2) |
| C2—C3 | 1.361 (7) | C18—H18 | 0.9300 |
| C2—C1 | 1.385 (7) | C19—C20 | 1.410 (9) |
| C2—H2 | 0.9300 | C20—C21 | 1.357 (11) |
| C7—N1 | 1.327 (6) | C20—H20 | 0.9300 |
| C7—C8 | 1.385 (8) | C21—C22 | 1.403 (10) |
| C7—H7 | 0.9300 | C21—H21 | 0.9300 |
| C8—C9 | 1.363 (7) | C22—C23 | 1.375 (8) |
| C8—H8 | 0.9300 | C22—H22 | 0.9300 |
| C9—C10 | 1.420 (6) | C23—H23 | 0.9300 |
| C9—H9 | 0.9300 | N3—H3A | 0.8600 |
| C10—C6 | 1.396 (6) | O1—H1A | 0.91 (8) |
| C10—C11 | 1.425 (6) | C1—N2 | 1.322 (6) |
| C11—N3 | 1.375 (6) | C1—H1 | 0.9300 |
| C11—C12 | 1.381 (6) | C3—C4 | 1.402 (6) |
| C13—N4 | 1.337 (6) | C3—H3 | 0.9300 |
| C13—N3 | 1.378 (6) | C4—C5 | 1.396 (7) |
| C13—C14 | 1.463 (6) | C4—C12 | 1.427 (6) |
| C14—C15 | 1.391 (7) | C5—N2 | 1.374 (6) |
| C14—C16 | 1.425 (7) | C5—C6 | 1.456 (6) |
| C15—O1 | 1.355 (7) | C6—N1 | 1.354 (6) |
| C15—C17 | 1.407 (8) | C12—N4 | 1.376 (6) |
| C16—C23 | 1.409 (8) | N1—Hg1 | 2.486 (4) |
| C16—C19 | 1.425 (7) | N2—Hg1 | 2.391 (4) |
| C17—C18 | 1.358 (9) | Hg1—I2 | 2.6435 (4) |
| C17—H17 | 0.9300 | Hg1—I1 | 2.6912 (5) |
| C18—C19 | 1.389 (9) | ||
| C3—C2—C1 | 119.2 (5) | C20—C21—H21 | 119.3 |
| C3—C2—H2 | 120.4 | C22—C21—H21 | 119.3 |
| C1—C2—H2 | 120.4 | C23—C22—C21 | 118.9 (7) |
| N1—C7—C8 | 123.2 (5) | C23—C22—H22 | 120.6 |
| N1—C7—H7 | 118.4 | C21—C22—H22 | 120.6 |
| C8—C7—H7 | 118.4 | C22—C23—C16 | 121.7 (6) |
| C9—C8—C7 | 119.4 (5) | C22—C23—H23 | 119.2 |
| C9—C8—H8 | 120.3 | C16—C23—H23 | 119.2 |
| C7—C8—H8 | 120.3 | C11—N3—C13 | 107.6 (4) |
| C8—C9—C10 | 118.5 (5) | C11—N3—H3A | 126.2 |
| C8—C9—H9 | 120.8 | C13—N3—H3A | 126.2 |
| C10—C9—H9 | 120.8 | C15—O1—H1A | 103 (5) |
| C6—C10—C9 | 118.6 (5) | N2—C1—C2 | 123.9 (5) |
| C6—C10—C11 | 116.9 (4) | N2—C1—H1 | 118.1 |
| C9—C10—C11 | 124.5 (4) | C2—C1—H1 | 118.1 |
| N3—C11—C12 | 105.5 (4) | C2—C3—C4 | 118.9 (5) |
| N3—C11—C10 | 132.4 (4) | C2—C3—H3 | 120.5 |
| C12—C11—C10 | 122.1 (4) | C4—C3—H3 | 120.5 |
| N4—C13—N3 | 110.6 (4) | C5—C4—C3 | 119.0 (4) |
| N4—C13—C14 | 122.6 (4) | C5—C4—C12 | 117.1 (4) |
| N3—C13—C14 | 126.5 (4) | C3—C4—C12 | 123.9 (5) |
| C15—C14—C16 | 119.7 (5) | N2—C5—C4 | 121.1 (4) |
| C15—C14—C13 | 116.7 (4) | N2—C5—C6 | 118.1 (4) |
| C16—C14—C13 | 123.6 (4) | C4—C5—C6 | 120.8 (4) |
| O1—C15—C14 | 122.6 (5) | N1—C6—C10 | 121.4 (5) |
| O1—C15—C17 | 117.0 (5) | N1—C6—C5 | 117.7 (4) |
| C14—C15—C17 | 120.3 (6) | C10—C6—C5 | 120.9 (4) |
| C23—C16—C19 | 118.4 (5) | N4—C12—C11 | 110.6 (4) |
| C23—C16—C14 | 123.7 (5) | N4—C12—C4 | 127.6 (4) |
| C19—C16—C14 | 117.8 (5) | C11—C12—C4 | 121.7 (4) |
| C18—C17—C15 | 120.4 (6) | C7—N1—C6 | 118.8 (5) |
| C18—C17—H17 | 119.8 | C7—N1—Hg1 | 125.3 (3) |
| C15—C17—H17 | 119.8 | C6—N1—Hg1 | 115.0 (3) |
| C17—C18—C19 | 120.8 (6) | C1—N2—C5 | 117.9 (4) |
| C17—C18—H18 | 119.6 | C1—N2—Hg1 | 124.2 (3) |
| C19—C18—H18 | 119.6 | C5—N2—Hg1 | 117.6 (3) |
| C18—C19—C20 | 120.6 (6) | C13—N4—C12 | 105.6 (4) |
| C18—C19—C16 | 120.6 (6) | N2—Hg1—N1 | 68.14 (14) |
| C20—C19—C16 | 118.8 (7) | N2—Hg1—I2 | 107.31 (9) |
| C21—C20—C19 | 120.8 (7) | N1—Hg1—I2 | 109.47 (10) |
| C21—C20—H20 | 119.6 | N2—Hg1—I1 | 116.46 (9) |
| C19—C20—H20 | 119.6 | N1—Hg1—I1 | 96.33 (9) |
| C20—C21—C22 | 121.4 (7) | I2—Hg1—I1 | 135.010 (15) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N3—H3A···I1i | 0.86 | 3.05 | 3.896 (4) | 167. |
| O1—H1A···N4 | 0.91 (8) | 1.77 (8) | 2.623 (6) | 155 (7) |
| Symmetry codes: (i) −x+1, −y+1, −z. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N3—H3A···I1i | 0.86 | 3.05 | 3.896 (4) | 167. |
| O1—H1A···N4 | 0.91 (8) | 1.77 (8) | 2.623 (6) | 155 (7) |
| Symmetry codes: (i) −x+1, −y+1, −z. |
The author thanks Guangdong University of Petrochemical Technology for supporting this work.
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Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Wang, X. Y., Ma, X. Y., Liu, Y., Xu, Z. L. & Kong, Z. G. (2010). Chin. J. Inorg. Chem. 26, 1482–1484.
The ligand 1-(1H-imidazo[4,5-f][1,10]phenanthrolin-2-yl)naphthalen-2-ol) is a N-donor ligand and has excellent coordinating ability (Wang et al., 2010). In this work, we selected it as an N-donor chelating ligand, generating a new HgII complex.
In the compound, the central HgII atom is four-coordinated by two N atoms from one organic ligand, and two I atoms in a distorted tetrahedral sphere. N-H···I and O-H···N H-bonding interactions stabilize the crystal structure and the molecular conformation.